DE2356812C3 - Herbicidal agent based on mixtures with phenoxynitrobenzoic acid derivatives - Google Patents
Herbicidal agent based on mixtures with phenoxynitrobenzoic acid derivativesInfo
- Publication number
- DE2356812C3 DE2356812C3 DE19732356812 DE2356812A DE2356812C3 DE 2356812 C3 DE2356812 C3 DE 2356812C3 DE 19732356812 DE19732356812 DE 19732356812 DE 2356812 A DE2356812 A DE 2356812A DE 2356812 C3 DE2356812 C3 DE 2356812C3
- Authority
- DE
- Germany
- Prior art keywords
- mixtures
- phenoxynitrobenzoic
- acid derivatives
- herbicidal agent
- days
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000203 mixture Substances 0.000 title claims description 13
- 239000004009 herbicide Substances 0.000 title claims description 10
- WDYOOOAKXRCRPZ-UHFFFAOYSA-N 2-nitro-3-phenoxybenzoic acid Chemical class OC(=O)C1=CC=CC(OC=2C=CC=CC=2)=C1[N+]([O-])=O WDYOOOAKXRCRPZ-UHFFFAOYSA-N 0.000 title 1
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- PKRSYEPBQPFNRB-UHFFFAOYSA-N 2-phenoxybenzoic acid Chemical class OC(=O)C1=CC=CC=C1OC1=CC=CC=C1 PKRSYEPBQPFNRB-UHFFFAOYSA-N 0.000 claims 2
- 229940126062 Compound A Drugs 0.000 description 9
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 8
- 230000002363 herbicidal effect Effects 0.000 description 8
- 230000002195 synergetic effect Effects 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 5
- VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical class ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 description 4
- 240000008620 Fagopyrum esculentum Species 0.000 description 4
- 235000009419 Fagopyrum esculentum Nutrition 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- -1 phenoxybenzoate ester Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 235000011293 Brassica napus Nutrition 0.000 description 2
- 240000008100 Brassica rapa Species 0.000 description 2
- 235000000540 Brassica rapa subsp rapa Nutrition 0.000 description 2
- 241000287828 Gallus gallus Species 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 235000017016 Setaria faberi Nutrition 0.000 description 2
- 241000820191 Setaria magna Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 244000062793 Sorghum vulgare Species 0.000 description 2
- 235000012343 cottonseed oil Nutrition 0.000 description 2
- 244000038559 crop plants Species 0.000 description 2
- 235000019713 millet Nutrition 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- 229910021532 Calcite Inorganic materials 0.000 description 1
- 244000068645 Carya illinoensis Species 0.000 description 1
- 235000009025 Carya illinoensis Nutrition 0.000 description 1
- 244000239348 Echinochloa crus galli var. praticola Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical group O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000002006 petroleum coke Substances 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Es sind synergistische Herbicidgemische von verschiedenen Diphenyläthern mit weiteren Triazin-, Thiocarbamat-, Anilid- und Harnstoffherbiciden bekannt, wie sie beispielsweise in der US-PS 36 71 216 angegeben sind. Andere synergistische Herbicidgemische enthalten Chloracetanilidderivate (US-PS 35 51 132, 3442 945, 33 93 991). Diese Mittel genügen jedoch nicht immer allen Anforderungen. Es wurde nun ein herbizides Mittel gefunden, welches nicht nur die Vorteile der unlängst bekanntgewordenen Phenoxyniirobenzoesäurederviate mit denen der Chloracetanilidderivate vereinigt, sondern darüber hinaus synergistische Wirkungssteigerungen aufweist. Dieses Mittel ist in den Patentansprüchen gekennzeichnet. Eine Komponente der herbiziden Mittel gemäß der Erfindung besteht aus einer Herbicidverbindung der FormelThere are synergistic herbicide mixtures of different diphenyl ethers with other triazine, Thiocarbamate, anilide and urea herbicides known, as indicated, for example, in US Pat. No. 3,671,216. Other synergistic herbicide mixtures contain chloroacetanilide derivatives (US-PS 35 51 132, 3442 945, 33 93 991). These funds are sufficient however, not always all requirements. It has now been found a herbicidal agent which not only the Advantages of the recently known phenoxynirobenzoic acid derivatives with those of the chloroacetanilide derivatives combined, but also has synergistic increases in effectiveness. This remedy is in characterized by the claims. A component of the herbicidal compositions according to the invention consists of a herbicide compound of the formula
CORCOR
O2NO 2 N
worin X ein Halogenatom, π die Zahlen 1 bis 5 und R eine Hydroxyl-, Alkoxy- (Ci—Cj) oder Phenoxygruppe bedeuten.where X is a halogen atom, π is the numbers 1 to 5 and R is a hydroxyl, alkoxy (Ci-Cj) or phenoxy group.
Diese Verbindungen und ihre Herstellung sind im einzelnen in der US-PS 36 52 645 angegeben. Alle dort beschriebenen Wirkstoffbeispiele sind, soweit sie unter die Patentansprüche der vorliegenden Erfindung fallen, als Komponenten geeignet.These compounds and their preparation are detailed in US Pat. No. 3,652,645. All there Examples of active ingredients described are, insofar as they come under the claims of the present invention, suitable as components.
Von besonderem Interesse sind hier von den in der US-PS 36 52 645 beschriebenen Wirkstoffen die folgenden Verbindungen, welche durch die Buchstaben A, B und C nachfolgend angegeben werden:Of particular interest here of the active ingredients described in US Pat. No. 3,652,645 are the following Compounds indicated by the letters A, B and C below:
(A) Methyl-(2-nitro)-[5-(2',4'-dichlorphenoxy)]-benzoat, (A) methyl (2-nitro) - [5- (2 ', 4'-dichlorophenoxy)] benzoate,
(B) Methyl-(2-nitro)-[5-(2',4',6'-trichlorphenoxy)]-benzoat, (B) methyl (2-nitro) - [5- (2 ', 4', 6'-trichlorophenoxy)] benzoate,
(C) Methyl-(2-nitro)-[5-(2',4'-dichlor-6'-fluorphenoxy)]-benzoat. (C) Methyl (2-nitro) - [5- (2 ', 4'-dichloro-6'-fluorophenoxy)] benzoate.
Die Verbindung A erwies sich als besonders wirksam. Die andere Komponente der synergistischen Zusammensetzungen gemäß der Erfindung besteht aus einer der handelsüblichen herbicid wirksamen Chloracetanilidverbindungen: Compound A was found to be particularly effective. The other component of the synergistic compositions according to the invention consists of one of the commercially available herbicidally active chloroacetanilide compounds:
2-Chlor N-isopropylacetanilid2-chloro N-isopropyl acetanilide
(Ramrod) oder
2-Chlor-2',6'-diäthyl-N-(methoxy-methyl)-acetanilid(Ramrod) or
2-chloro-2 ', 6'-diethyl-N- (methoxy-methyl) -acetanilide
(Lasso)(Lasso)
Kombinationen der Verbindung A mit Ramrod oder Lasso können bei der allgemeinen Unkrautbekämpfung wirksam sein. In der Praxis wird die Herbicidauftragung in Kilogramm je 1000 m2 angegeben. Die Gemische gemäß der Erfindung sind wirksam, wenn sie in Mengen zwischen etwa 0,23 und etwa 4,54 kg Wirkstoffgemisch je 4050 m2 aufgetragen werden. Im Gemisch beträgt das Gewichtsverhältnis des Phenoxybenzoatesters zu dem Chloracetanilidderivat etwa 0,5 :4 bis etwa 4 :0,5, vorzugsweise etwa 1 :1.Combinations of Compound A with Ramrod or Lasso can be effective in general weed control. In practice, the herbicide application is given in kilograms per 1000 m 2 . The mixtures according to the invention are effective when they are applied in amounts between about 0.23 and about 4.54 kg of active ingredient mixture per 4050 m 2 . In the mixture, the weight ratio of the phenoxybenzoate ester to the chloroacetanilide derivative is about 0.5: 4 to about 4: 0.5, preferably about 1: 1.
Die synergistischen Wirkstoffgemische gemäß der Erfindung können in verschiedenen Weisen angewendet werden. Sie können als solche, und zwar als Feststoffe oder in verdampfter Form aufgetragen werden, werden jedoch vorzugsweise in Form von pesticid wirksamen Massen aus Wirkstoffen und einem Träger aufgebracht. Die Massen können als Granulate, Stäube oder flüssige Besprühungen oder als gasgetriebene Besprühungen aufgebracht werden und können außer dem Träger Zusätze wie Emulgiermittel, Bindemittel, zum flüssigen Zustand komprimierte Gase, Geruchsmittel, Stabilisatoren und dergleichen enthalten. Eine große Vielzahl von flüssigen und festen Trägern könen verwendet werden. Beispiele für feste Träger sind Talk, Bentonit, Diatomeenerde, Pyrophyllit, Fullererde, Gips, sich von Baumwollsamen und Nußschalen ableitende Mehle und verschiedene natürliche und synthetische Tone mit einem pH-Wert nicht oberhalb etwa 9,5. Andere feste Träger können aus Sand, Maiskolben, Attapulgit, Montmorillonit, Erdölkoks, Calcit, Pecanschalen und Furfurolrückständen bestehen. Beispiele für flüssige Träger sind Wasser, organische Lösungsmittel wie Alkohole, Ketone, Halogenaromaten, Amide und Ester, Mineralöle (wie Kerosin, Leichtöle und Mittelöle) undThe synergistic active ingredient mixtures according to the invention can be used in various ways will. They can be applied as such, namely as solids or in vaporized form but preferably applied in the form of pesticidally active compositions of active ingredients and a carrier. The masses can be as granules, dusts or liquid sprays or as gas-powered sprays can be applied and, in addition to the carrier, additives such as emulsifiers, binders, to the liquid Condition contain compressed gases, odorants, stabilizers and the like. A great variety of liquid and solid carriers can be used. Examples of solid carriers are talc, bentonite, diatomaceous earth, Pyrophyllite, fuller's earth, gypsum, flours derived from cottonseed and nutshells and various natural and synthetic clays with a pH not above about 9.5. Other festivals Carriers can be made from sand, corn on the cob, attapulgite, montmorillonite, petroleum coke, calcite, and pecan shells Furfural residues exist. Examples of liquid carriers are water, organic solvents such as Alcohols, ketones, halogenated aromatics, amides and esters, mineral oils (such as kerosene, light oils and middle oils) and
pflanzliche Öle (wie Baumwollsamenöl).vegetable oils (such as cottonseed oil).
Wie nachfolgend angegeben, zeigt ein Gemisch aus der Verbindung A in einer Menge von 0,34 kg je 4050 m2 As indicated below, shows a mixture of compound A in an amount of 0.34 kg per 4050 m 2
so in Kombination mit einem handelsüblichen Herbicid in einer Menge von 0,34 kg je 4050 m2 eine größere Wirksamkeit gegen bestimmte Unkrautarten als wenn jede Komponente allein in einer Menge von 0,68 kg je 4050 m2 untersucht wurde, was einen synergistischen Effekt darstellt.so in combination with a commercial herbicide in an amount of 0.34 kg per 4050 m 2 a greater effectiveness against certain weed species than when each component was examined alone in an amount of 0.68 kg per 4050 m 2 , which represents a synergistic effect .
Sämtliche Nutzpflanzen- und Unkrautarten wurden in Metallgewächshausflachkästen (Fläche etwa 0,093 m2), die Topferde enthielten, gepflanzt. Die Nutzpflanzensamen wurden in Rillen gepflanzt. Die Unkrautarten wurden in getrennte abgegrenzte Bereiche auf der Oberfläche der Flachschalen gesät und mit .gesiebtem Boden in ausreichender Menge zur Abdekkung der Samen bestäubt. Die gesamte Bewässerung erfolgte unter der Erdoberfläche.All crops and weeds were planted in metal greenhouse flat boxes (area about 0.093 m 2 ) containing potting soil. The crop seeds were planted in grooves. The weed species were sown in separate demarcated areas on the surface of the shallow trays and pollinated with sieved soil in sufficient quantity to cover the seeds. All irrigation was done underground.
Die Sprühbehandlungen erfolgten in einer Haube, die eine bewegliche Sprühdüse hatte. Die behandelten Pflanzen wurden in das Gewächshaus nach dem Besprühen gebracht. 6 Tage und 14 Tage nach derThe spray treatments were carried out in a hood that had a movable spray nozzle. The treated Plants were brought into the greenhouse after spraying. 6 days and 14 days after the
Behandlung wurde die prozentuale Vorauflaufschädigung oder -bekämpfung visuell bewertet.Treatment, percent pre-emergence damage or control was assessed visually.
Teste wurden mit der Verbindung A (0,68 kg/ 4050 m2), »Lasso« (0,68 kg/4050 m2) und »Ramrod« (0,68 kg/4050 m2) durchgeführt. Teste wurden auch mit Kombinationen der Verbindung A (034 kg/4050 m2)Tests were carried out with compound A (0.68 kg / 4050 m 2 ), "Lasso" (0.68 kg / 4050 m 2 ) and "Ramrod" (0.68 kg / 4050 m 2 ). Tests were also carried out with combinations of compound A (034 kg / 4050 m 2 ) und »Ramrod« (034 kg/4050 m2) bzw. der Verbindung A (0,34 kg/4050 m2) und »Lasso« (0,34 kg/4050 m2) durchgeführt Die prozentuale Schädigung oder Bekämpfung für jede Pflanzenart ergibt sich aus der Tabelle.and "Ramrod" (034 kg / 4050 m 2 ) or compound A (0.34 kg / 4050 m 2 ) and "Lasso" (0.34 kg / 4050 m 2 ) The percentage damage or control for each plant species results from the table.
Kombinationen (0,34 kg/4050 m2 + 0,34 kg/4050 m2) Zeit der BewertungCombinations (0.34 kg / 4050 m 2 + 0.34 kg / 4050 m 2 ) Time of evaluation
Verbindung A + »Ramrod« Verbindung A + »Lasso« Tage 14 Tage 6 Tage 14 TageConnection A + "Ramrod" Connection A + "Lasso" Days 14 days 6 days 14 days
Wie sich aus den Werten der Tabelle ergibt, wurde eine synergistische Aktivität für die Kombination der Verbindung A und »Ramrod« gegen BuchweizenAs can be seen from the values in the table, a synergistic activity was found for the combination of Compound A and "Ramrod" against buckwheat gezeigt. Die Kombination der Verbindung A und »Lasso« zeigte eine synergistische Aktivität gegen Hühnerhirse, Grieswurz und Buchweizen.shown. The combination of compound A and "Lasso" showed a synergistic activity against barnyard millet, semolina and buckwheat.
Es wurde ein Test mit den Verbindungen A (Methyl-(2-nitro)-[5-(2',4'-dichlorphenoxy)]-benzoat)bei einer Rate von 0,34 kg/4050 m2 und »Ramrod« (2-Chlor-N-isopropylacetanilid) bei einer Rate von 0,68 kg/ 4050 m2 gegen Winde durchgeführt.A test was carried out with the compounds A (methyl (2-nitro) - [5- (2 ', 4'-dichlorophenoxy)] benzoate) at a rate of 0.34 kg / 4050 m 2 and "Ramrod" ( 2-chloro-N-isopropylacetanilide) carried out against winds at a rate of 0.68 kg / 4050 m 2.
»Ramrod« allein war bei diesem Versuch wirksam. Die"Ramrod" alone was effective in this attempt. the
»Ramrod«) ergab jedoch eine herbicide Wirksamkeit"Ramrod"), however, showed a herbicidal activity von 33.from 33.
Claims (2)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30769372A | 1972-11-17 | 1972-11-17 | |
| US37246373A | 1973-06-21 | 1973-06-21 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2356812A1 DE2356812A1 (en) | 1974-06-06 |
| DE2356812B2 DE2356812B2 (en) | 1980-11-27 |
| DE2356812C3 true DE2356812C3 (en) | 1981-11-05 |
Family
ID=26975884
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732356812 Expired DE2356812C3 (en) | 1972-11-17 | 1973-11-14 | Herbicidal agent based on mixtures with phenoxynitrobenzoic acid derivatives |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS49133524A (en) |
| AR (1) | AR215827A1 (en) |
| CA (1) | CA1018790A (en) |
| CH (1) | CH578319A5 (en) |
| DE (1) | DE2356812C3 (en) |
| FR (1) | FR2206906B1 (en) |
| GB (1) | GB1412660A (en) |
| IT (1) | IT1048155B (en) |
| NL (1) | NL175780C (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0001328A1 (en) * | 1977-09-23 | 1979-04-04 | FISONS plc | Method and composition for combating weeds |
| IL57767A (en) * | 1978-07-15 | 1982-02-28 | Lilly Industries Ltd | Herbicidal method and synergistic compositions comprising a phenoxybenzoic acid derivative and a phenoxyalkanoic acid derivative |
| CA1129665A (en) * | 1978-12-21 | 1982-08-17 | James L. Glasgow | Method of combating weeds in cereal crops and herbicidal formulation therefor |
| CH645515A5 (en) * | 1981-02-19 | 1984-10-15 | Siegfried Ag | MEDIA FOR LEAVING CULTIVATED PLANTS. |
| DE3129432A1 (en) * | 1981-07-25 | 1983-02-10 | Norddeutsche Affinerie AG, 2000 Hamburg | MEANS FOR SELECTIVE WEED CONTROL AND ITS APPLICATION |
| ATE14364T1 (en) * | 1981-11-07 | 1985-08-15 | Siegfried Ag | METHOD OF CONTROL OF A BROAD RANGE OF WEEDS IN CROPS AND COMPOSITION FOR THAT METHOD. |
| DE3223013A1 (en) * | 1982-06-19 | 1983-12-22 | Norddeutsche Affinerie AG, 2000 Hamburg | MEANS FOR SELECTIVE WEED CONTROL |
| EP4568485A1 (en) * | 2022-08-10 | 2025-06-18 | Adama Agan Ltd. | Herbicidal composition comprising bifenox and vlcfa inhibitor |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3652645A (en) * | 1969-04-25 | 1972-03-28 | Mobil Oil Corp | Halophenoxy benzoic acid herbicides |
-
1973
- 1973-11-09 NL NL7315417A patent/NL175780C/en not_active IP Right Cessation
- 1973-11-13 AR AR25098173A patent/AR215827A1/en active
- 1973-11-14 DE DE19732356812 patent/DE2356812C3/en not_active Expired
- 1973-11-14 IT IT3130373A patent/IT1048155B/en active
- 1973-11-15 CH CH1608573A patent/CH578319A5/xx not_active IP Right Cessation
- 1973-11-15 JP JP12777073A patent/JPS49133524A/ja active Pending
- 1973-11-16 GB GB5319573A patent/GB1412660A/en not_active Expired
- 1973-11-16 CA CA185,963A patent/CA1018790A/en not_active Expired
- 1973-11-16 FR FR7341009A patent/FR2206906B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2356812A1 (en) | 1974-06-06 |
| IT1048155B (en) | 1980-11-20 |
| AU6257873A (en) | 1975-05-22 |
| CH578319A5 (en) | 1976-08-13 |
| DE2356812B2 (en) | 1980-11-27 |
| FR2206906B1 (en) | 1978-03-10 |
| GB1412660A (en) | 1975-11-05 |
| NL175780C (en) | 1985-01-02 |
| JPS49133524A (en) | 1974-12-21 |
| CA1018790A (en) | 1977-10-11 |
| FR2206906A1 (en) | 1974-06-14 |
| NL7315417A (en) | 1974-05-21 |
| AR215827A1 (en) | 1979-11-15 |
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